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72-44-6

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Basic Information
CAS No.: 72-44-6
Name: METHAQUALONE
Article Data: 60
Molecular Structure:
Molecular Structure of 72-44-6 (METHAQUALONE)
Formula: C16H14N2O
Molecular Weight: 250.3
Synonyms: 4(3H)-Quinazolinone,2-methyl-3-o-tolyl- (6CI,8CI);(2-Methyl-3-(o-tolyl)-3,4-dihydro-4-(quinazolinone);(?à)-Methaqualone;2-Methyl-3-(o-tolyl)quinazolone;2-Methyl-3-o-tolyl-4(3H)-chinazolone;2-Methyl-3-o-tolyl-4(3H)-quinazolinone;2-Methyl-3-o-tolyl-4-quinazolone;2-Methyl-3-o-tolylquinazolin-4-one;2-Methyl-3-tolyl-4-oxybensdiazine;3,4-Dihydro-2-methyl-4-oxo-3-o-tolylquinazoline;CI-705;CN 38703;Cateudyl;Citexal;Dormigoa;Dormogen;Dormutil;Dorsedin;Fadormir;Holodorm;Hyminal;Hypcol;Hypocol;Hyptor;Hyptor base;Ipnofil;MAOA;MTQ;Melsed;Melsedinbase;Melsomin;Mequin;Metakvalon;Metaqualon;Methaqualon;Methaqualone;Methaqualoneinone;Metolquizolone;Mollinox;Motolon;Mozambin;NSC 111388;NSC126877;NSC 631628;Nobedorm;Noctilene;Normi-Nox;Omnyl;Optinoxan;Orthonal;Ortonal;Parminal;QZ 2;Quaalude;Qua.hivin.a.hivin.lude;R 148;RIC 272;Revonal;Rorer 148;Rorer 714;Roulone;Rouqualone;Sindesvel;Somberol;Somnafac;Somnomed;Sonal;Sopor;Soverin;TR 495;Torinal;Tuazol;Tuazole;Tuazolone;
EINECS: 200-780-4
Density: 1.16 g/cm3
Melting Point: 120ºC
Boiling Point: 406.9 °C at 760 mmHg
Flash Point: 199.9 °C
Solubility: 299.9mg/L(23 oC)
Hazard Symbols: FlammableF,ToxicT
Risk Codes: 11-23/24/25-39/23/24/25
Safety: 7-16-36/37-45
PSA: 34.89000
LogP: 3.00250
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History

Methaqualone is a sedative drug .This drug is a general CNS depressant.In the 1960s and 1970s, it was used  as a hypnotic, for the treatment of insomnia, and as a sedative and muscle relaxant. It has also been used illegally as a recreational drug, commonly known as Quaaludes (particularly in the 1970s in North America) or as Mandrax (methaqualone 250 mgs combined with diphenhydramine 5 mg).It is widely used in South Africa in the 2000s.

Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The Methaqualone, with the CAS registry number 72-44-6, is also known as Methyl-o-tolylquinazolone. It belongs to the product categories of Controlled Drug Standards Alphabetic M; Meta-Meth; Stable Isotopes. Its EINECS registry number is 200-780-4. This chemical's molecular formula is C16H14N2O and molecular weight is 250.29516. Its IUPAC name is called 2-methyl-3-(2-methylphenyl)quinazolin-4-one. Methaqualone is a sedative-hypnotic drug that is similar in effect to barbiturates, a general central nervous system depressant. Its use peaked in the 1960s and 1970s as a hypnotic, for the treatment of insomnia, and as a sedative and muscle relaxant. It has also been used illegally as a recreational drug, commonly known as Quaaludes, Sopors, Ludes or Mandrax depending on the manufacturer. Since at least 2001, it has been widely used in South Africa, where it is commonly referred to as "smarties" or "geluk-tablette". 

Physical properties of Methaqualone: (1)ACD/LogP: 2.50; (2)ACD/LogD (pH 5.5): 2.5; (3)ACD/LogD (pH 7.4): 2.5; (4)ACD/BCF (pH 5.5): 46.64; (5)ACD/BCF (pH 7.4): 46.77; (6)ACD/KOC (pH 5.5): 544.21; (7)ACD/KOC (pH 7.4): 545.74; (8)#H bond acceptors: 3; (9)#Freely Rotating Bonds: 1; (10)Index of Refraction: 1.623; (11)Molar Refractivity: 76.12 cm3; (12)Molar Volume: 215.6 cm3; (13)Surface Tension: 42.9 dyne/cm; (14)Density: 1.16 g/cm3; (15)Flash Point: 199.9 °C; (16)Enthalpy of Vaporization: 65.87 kJ/mol; (17)Boiling Point: 406.9 °C at 760 mmHg; (18)Vapour Pressure: 7.86E-07 mmHg at 25°C.

Preparation of Methaqualone: this chemical can be prepared by 2-acetylamino-benzoic acid and 2-methyl-aniline. This reaction will need reagents PCl3 and toluene.

Methaqualone can be prepared by 2-acetylamino-benzoic acid and 2-methyl-aniline

Uses of Methaqualone: it can be used to produce 2-phenacyl-3-o-tolyl-4(3H)-quinazolinone by heating. This reaction will need reagent NaH and solvent 1,2-dimethoxy-ethane with reaction time of 5 hours. The yield is about 80%.

Methaqualone can be used to produce 2-phenacyl-3-o-tolyl-4(3H)-quinazolinone by heating

When you are using this chemical, please be cautious about it as the following:
This chemical, which is toxic by inhalation, in contact with skin and if swallowed, is highly flammable. There will be a danger of very serious irreversible effects. You should keep it away from sources of ignition - No smoking. Whenever you will contact it, please wear suitable protective clothing and gloves. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CC1=CC=CC=C1N2C(=NC3=CC=CC=C3C2=O)C
(2)InChI: InChI=1S/C16H14N2O/c1-11-7-3-6-10-15(11)18-12(2)17-14-9-5-4-8-13(14)16(18)19/h3-10H,1-2H3
(3)InChIKey: JEYCTXHKTXCGPB-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 intraperitoneal 235mg/kg (235mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: ATAXIA

GASTROINTESTINAL: NAUSEA OR VOMITING
Farmakologiya i Toksikologiya Vol. 27, Pg. 413, 1964.
human TDLo oral 57mg/kg (57mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

GASTROINTESTINAL: NAUSEA OR VOMITING
Archiv fuer Toxikologie. Vol. 20, Pg. 31, 1963.
man LDLo oral 114mg/kg (114mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA
Archiv fuer Toxikologie. Vol. 20, Pg. 31, 1963.
mouse LD50 intraperitoneal 180mg/kg (180mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: STIFFNESS
Indian Journal of Medical Research. Vol. 69, Pg. 1008, 1979.
mouse LD50 oral 420mg/kg (420mg/kg)   Toxicology and Applied Pharmacology. Vol. 1, Pg. 42, 1959.
mouse LD50 parenteral 500mg/kg (500mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: ANALGESIA
Pharmaceutical Chemistry Journal Vol. 7, Pg. 626, 1973.
rabbit LD50 intravenous 100mg/kg (100mg/kg)   Archiv fuer Toxikologie. Vol. 20, Pg. 31, 1963.
rat LD50 intraperitoneal 125mg/kg (125mg/kg)  

Arzneimittel-Forschung. Drug Research. Vol. 17, Pg. 242, 1967.

rat LD50 oral 185mg/kg (185mg/kg)   Journal of Medicinal Chemistry. Vol. 24, Pg. 490, 1981.